##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_journal_date_recd_electronic     2022-08-02
_journal_date_accepted     2022-08-25
_journal_name_full     'IUCrData'
_journal_year     2022
_journal_volume     7
_journal_issue      8
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HM
_journal_paper_doi     10.1107/S2414314622008549
_journal_coeditor_code     WM4171
_publ_contact_author_name     'Hiromasa Kurosaki'
_publ_contact_author_address
;
College of Pharmacy, Kinjo Gakuin University, 2-1723 Omori,
Nagoya 463-8521, Japan
;
_publ_contact_author_email     'h-kurosaki@kinjo-u.ac.jp'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '+81+52+798-0180'
_publ_section_title
;\
Bis(nitrato-κO)(1,4,8,11-tetraazacyclotetradecane-κ⁴N)\
zinc(II) methanol monosolvate
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ichimaru, Yoshimi' .
;
Faculty of Pharmaceutical Sciences, Shonan University of Medical Sciences,
16-48 Kamishinano, Totsuka-ku, Yokohama, Kanagawa 244-0806,
Japan
;
    'Kato, Koichi'
;
Corresponding author
;
;
Faculty of Pharmaceutical Sciences, Shonan University of Medical Sciences,
16-48 Kamishinano, Totsuka-ku, Yokohama, Kanagawa 244-0806,
Japan
;
    'Kurihara, Masaaki' .
;
Faculty of Pharmaceutical Sciences, Shonan University of Medical Sciences,
16-48 Kamishinano, Totsuka-ku, Yokohama, Kanagawa 244-0806,
Japan
;
    'Jin, Wanchun' .
;
College of Pharmacy, Kinjo Gakuin University, 2-1723 Omori, Nagoya 463-8521,
Japan
;
    'Koike, Tohru' .
;
Department of Functional Molecular Science,
Institute of Biochemical & Health Sciences, Hiroshima University, 1-2-3 Kasumi,
Minami-ku, Hiroshima 734-8553,
Japan
;
    'Kurosaki, Hiromasa'
;
;
;
College of Pharmacy, Kinjo Gakuin University, 2-1723 Omori, Nagoya 463-8521,
Japan
;
_publ_section_synopsis
;
The coordination of the central ZnII atoms in the two different Zn-cyclam
units is distorted octahedral.
;
_database_code_depnum_ccdc_archive     2193206
_chemical_name_systematic
;\
Bis(nitrato-κO)(1,4,8,11-tetraazacyclotetradecane-κ⁴N)\
zinc(II)] methanol monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H24 N6 O6 Zn, C H4 O'
_chemical_formula_sum     'C11 H28 N6 O7 Zn'
_chemical_formula_iupac     '[Zn (N O3)2 (C10 H24 N4)], C H4 O'
_chemical_formula_weight     421.76
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.3412(5)
_cell_length_b     9.4306(3)
_cell_length_c     12.7716(4)
_cell_angle_alpha     90
_cell_angle_beta     105.864(4)
_cell_angle_gamma     90
_cell_volume     1777.38(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4300
_cell_measurement_theta_min     2.9710
_cell_measurement_theta_max     68.2410
_cell_measurement_temperature     100.0
_exptl_crystal_description     block
_exptl_crystal_colour     'clear colourless'
_exptl_crystal_size_max     0.542
_exptl_crystal_size_mid     0.194
_exptl_crystal_size_min     0.086
_exptl_crystal_density_diffrn     1.576
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     888
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    10 1 -3 0.2985
    1 -5 4 0.0734
    0 -3 -7 0.0505
    9 2 -1 0.2815
    -10 -1 4 0.2283
    9 1 0 0.2792
    -1 4 -6 0.1184
    -1 5 -4 0.1089
    -9 2 2 0.1814
    -1 6 -1 0.1032
    -7 4 5 0.1447
    -1 6 3 0.0710
    6 5 1 0.1909
    0 5 5 0.0430
    0 3 7 0.0318
    0 1 8 0.0337
    0 -1 8 0.0359
    7 -2 3 0.2245
_exptl_absorpt_coefficient_mu     2.355
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_absorpt_correction_T_min     0.35593
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     100.0
_diffrn_source     ?
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type     'Rigaku XtaLAB Synergy-i'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.0
_diffrn_reflns_number     9899
_diffrn_reflns_av_R_equivalents     0.0783
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_theta_min     2.995
_diffrn_reflns_theta_max     68.336
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_refine_special_details
;
All hydrogen atoms were placed using a geometrical computation.
;
_reflns_number_total     3230
_reflns_number_gt     2568
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0732
_refine_ls_R_factor_gt     0.0627
_refine_ls_wR_factor_gt     0.1726
_refine_ls_wR_factor_ref     0.1876
_refine_ls_goodness_of_fit_ref     1.010
_refine_ls_restrained_S_all     1.010
_refine_ls_number_reflns     3230
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.1278P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     1.012
_refine_diff_density_min     -0.916
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Zn' 'Zn' -1.5491 0.6778
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Zn Zn1 1.000000 0.500000 0.500000 0.0174(3) Uani d 1 . .
    Zn Zn2 0.500000 0.500000 0.500000 0.0210(3) Uani d 1 . .
    O O1 0.90165(12) 0.6144(2) 0.57953(17) 0.0228(5) Uani d 1 . .
    O O4 0.41074(12) 0.4107(2) 0.60524(17) 0.0240(5) Uani d 1 . .
    O O3 0.77063(11) 0.6485(2) 0.60726(18) 0.0285(6) Uani d 1 . .
    O O2 0.83570(14) 0.4444(3) 0.6451(2) 0.0327(6) Uani d 1 . .
    N N4 0.60866(19) 0.5006(2) 0.6400(3) 0.0180(7) Uani d 1 . .
    H H4 0.664921 0.519254 0.617093 0.022 Uiso calc 1 . .
    O O7 0.81007(13) 0.9063(2) 0.4951(2) 0.0361(6) Uani d 1 . .
    H H7 0.812347 0.819336 0.516078 0.043 Uiso d 1 . .
    O O6 0.28873(13) 0.3907(2) 0.6578(2) 0.0392(7) Uani d 1 . .
    O O5 0.31960(14) 0.5903(2) 0.5959(2) 0.0373(7) Uani d 1 . .
    N N2 0.89281(18) 0.4685(3) 0.3604(2) 0.0212(6) Uani d 1 . .
    H H2 0.835219 0.491792 0.379058 0.025 Uiso calc 1 . .
    N N1 0.98381(15) 0.3061(3) 0.5702(2) 0.0214(6) Uani d 1 . .
    H H1 0.933487 0.318926 0.605250 0.026 Uiso calc 1 . .
    N N5 0.83550(14) 0.5680(3) 0.6110(2) 0.0174(6) Uani d 1 . .
    N N6 0.33879(16) 0.4640(3) 0.6198(2) 0.0203(6) Uani d 1 . .
    N N3 0.47857(15) 0.7086(2) 0.5418(2) 0.0206(6) Uani d 1 . .
    H H3 0.428178 0.705969 0.577575 0.025 Uiso calc 1 . .
    C C9 0.62304(18) 0.3673(3) 0.7042(2) 0.0228(7) Uani d 1 . .
    H H9A 0.570572 0.350872 0.733703 0.027 Uiso calc 1 . .
    H H9B 0.677734 0.377161 0.766423 0.027 Uiso calc 1 . .
    C C5 0.90590(18) 0.5758(3) 0.2809(2) 0.0273(7) Uani d 1 . .
    H H5A 0.849116 0.587691 0.221956 0.033 Uiso calc 1 . .
    H H5B 0.954085 0.544320 0.248060 0.033 Uiso calc 1 . .
    C C8 0.59354(18) 0.6245(3) 0.7040(2) 0.0241(7) Uani d 1 . .
    H H8A 0.650488 0.649443 0.759304 0.029 Uiso calc 1 . .
    H H8B 0.547153 0.601449 0.742138 0.029 Uiso calc 1 . .
    C C6 0.45112(18) 0.8098(3) 0.4500(2) 0.0243(7) Uani d 1 . .
    H H6A 0.501178 0.820272 0.415422 0.029 Uiso calc 1 . .
    H H6B 0.439699 0.903787 0.478126 0.029 Uiso calc 1 . .
    C C7 0.56169(17) 0.7496(3) 0.6268(2) 0.0242(7) Uani d 1 . .
    H H7A 0.548869 0.832283 0.668051 0.029 Uiso calc 1 . .
    H H7B 0.609813 0.776730 0.592444 0.029 Uiso calc 1 . .
    C C1 1.06750(19) 0.2846(3) 0.6595(3) 0.0286(7) Uani d 1 . .
    H H1A 1.116932 0.251144 0.629517 0.034 Uiso calc 1 . .
    H H1B 1.057015 0.211822 0.710621 0.034 Uiso calc 1 . .
    C C10 0.63455(18) 0.2400(3) 0.6356(2) 0.0243(7) Uani d 1 . .
    H H10A 0.658080 0.159721 0.685250 0.029 Uiso calc 1 . .
    H H10B 0.681107 0.263706 0.597912 0.029 Uiso calc 1 . .
    C C2 0.95855(19) 0.1838(3) 0.4955(3) 0.0294(8) Uani d 1 . .
    H H2A 0.947341 0.100243 0.536938 0.035 Uiso calc 1 . .
    H H2B 1.009659 0.160697 0.465025 0.035 Uiso calc 1 . .
    C C4 0.88514(18) 0.3207(3) 0.3175(3) 0.0298(8) Uani d 1 . .
    H H4A 0.940106 0.297254 0.294672 0.036 Uiso calc 1 . .
    H H4B 0.832302 0.314258 0.252673 0.036 Uiso calc 1 . .
    C C3 0.87418(19) 0.2135(3) 0.4024(3) 0.0316(8) Uani d 1 . .
    H H3A 0.853153 0.122895 0.364889 0.038 Uiso calc 1 . .
    H H3B 0.825874 0.247888 0.433994 0.038 Uiso calc 1 . .
    C C11 0.7259(2) 0.9615(4) 0.5002(3) 0.0329(7) Uani d 1 . .
    H H11A 0.676872 0.901659 0.457126 0.049 Uiso calc 1 . .
    H H11B 0.718800 1.058159 0.470901 0.049 Uiso calc 1 . .
    H H11C 0.723491 0.963070 0.576083 0.049 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Zn1 O1 . 2.3045(18) ?
    Zn1 O1 3_766 2.3045(18) ?
    Zn1 N2 . 2.090(3) ?
    Zn1 N2 3_766 2.090(3) ?
    Zn1 N1 3_766 2.081(2) ?
    Zn1 N1 . 2.081(2) ?
    Zn2 O4 3_666 2.3233(19) ?
    Zn2 O4 . 2.3232(19) ?
    Zn2 N4 3_666 2.085(3) ?
    Zn2 N4 . 2.085(3) ?
    Zn2 N3 . 2.087(2) ?
    Zn2 N3 3_666 2.087(2) ?
    O1 N5 . 1.267(3) ?
    O4 N6 . 1.272(3) ?
    O3 N5 . 1.242(3) ?
    O2 N5 . 1.244(4) ?
    N4 H4 . 1.0000 ?
    N4 C9 . 1.484(4) ?
    N4 C8 . 1.480(4) ?
    O7 H7 . 0.8603 ?
    O7 C11 . 1.410(4) ?
    O6 N6 . 1.228(3) ?
    O5 N6 . 1.245(4) ?
    N2 H2 . 1.0000 ?
    N2 C5 . 1.485(4) ?
    N2 C4 . 1.490(4) ?
    N1 H1 . 1.0000 ?
    N1 C1 . 1.480(4) ?
    N1 C2 . 1.480(4) ?
    N3 H3 . 1.0000 ?
    N3 C6 . 1.481(4) ?
    N3 C7 . 1.483(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C9 C10 . 1.524(4) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C5 C1 3_766 1.520(4) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C8 C7 . 1.530(4) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C6 C10 3_666 1.535(4) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C2 C3 . 1.525(4) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C4 C3 . 1.525(5) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 Zn1 O1 3_766 . 180.0 ?
    N2 Zn1 O1 3_766 . 90.86(9) ?
    N2 Zn1 O1 . 3_766 90.86(9) ?
    N2 Zn1 O1 . . 89.14(9) ?
    N2 Zn1 O1 3_766 3_766 89.14(9) ?
    N2 Zn1 N2 . 3_766 180.00(15) ?
    N1 Zn1 O1 3_766 3_766 92.98(8) ?
    N1 Zn1 O1 3_766 . 87.02(8) ?
    N1 Zn1 O1 . 3_766 87.02(8) ?
    N1 Zn1 O1 . . 92.98(8) ?
    N1 Zn1 N2 3_766 3_766 94.81(10) ?
    N1 Zn1 N2 . 3_766 85.19(10) ?
    N1 Zn1 N2 3_766 . 85.19(10) ?
    N1 Zn1 N2 . . 94.81(10) ?
    N1 Zn1 N1 . 3_766 180.00(12) ?
    O4 Zn2 O4 . 3_666 180.0 ?
    N4 Zn2 O4 3_666 3_666 87.95(9) ?
    N4 Zn2 O4 . 3_666 92.05(9) ?
    N4 Zn2 O4 3_666 . 92.05(9) ?
    N4 Zn2 O4 . . 87.95(9) ?
    N4 Zn2 N4 3_666 . 180.0 ?
    N4 Zn2 N3 3_666 . 94.42(9) ?
    N4 Zn2 N3 . 3_666 94.42(9) ?
    N4 Zn2 N3 3_666 3_666 85.58(9) ?
    N4 Zn2 N3 . . 85.58(9) ?
    N3 Zn2 O4 3_666 . 88.02(8) ?
    N3 Zn2 O4 . . 91.98(8) ?
    N3 Zn2 O4 3_666 3_666 91.98(8) ?
    N3 Zn2 O4 . 3_666 88.02(8) ?
    N3 Zn2 N3 . 3_666 180.0 ?
    N5 O1 Zn1 . . 130.97(17) ?
    N6 O4 Zn2 . . 127.85(18) ?
    Zn2 N4 H4 . . 107.5 ?
    C9 N4 Zn2 . . 115.77(18) ?
    C9 N4 H4 . . 107.5 ?
    C8 N4 Zn2 . . 105.45(18) ?
    C8 N4 H4 . . 107.5 ?
    C8 N4 C9 . . 112.7(3) ?
    C11 O7 H7 . . 107.3 ?
    Zn1 N2 H2 . . 107.8 ?
    C5 N2 Zn1 . . 105.34(18) ?
    C5 N2 H2 . . 107.8 ?
    C5 N2 C4 . . 113.4(3) ?
    C4 N2 Zn1 . . 114.27(19) ?
    C4 N2 H2 . . 107.8 ?
    Zn1 N1 H1 . . 106.5 ?
    C1 N1 Zn1 . . 105.80(17) ?
    C1 N1 H1 . . 106.5 ?
    C2 N1 Zn1 . . 116.65(18) ?
    C2 N1 H1 . . 106.5 ?
    C2 N1 C1 . . 114.1(2) ?
    O3 N5 O1 . . 118.6(2) ?
    O3 N5 O2 . . 120.8(2) ?
    O2 N5 O1 . . 120.6(2) ?
    O6 N6 O4 . . 119.8(3) ?
    O6 N6 O5 . . 120.3(2) ?
    O5 N6 O4 . . 119.9(2) ?
    Zn2 N3 H3 . . 106.8 ?
    C6 N3 Zn2 . . 115.81(18) ?
    C6 N3 H3 . . 106.8 ?
    C6 N3 C7 . . 114.4(2) ?
    C7 N3 Zn2 . . 105.63(17) ?
    C7 N3 H3 . . 106.8 ?
    N4 C9 H9A . . 109.2 ?
    N4 C9 H9B . . 109.2 ?
    N4 C9 C10 . . 111.9(2) ?
    H9A C9 H9B . . 107.9 ?
    C10 C9 H9A . . 109.2 ?
    C10 C9 H9B . . 109.2 ?
    N2 C5 H5A . . 110.0 ?
    N2 C5 H5B . . 110.0 ?
    N2 C5 C1 . 3_766 108.4(2) ?
    H5A C5 H5B . . 108.4 ?
    C1 C5 H5A 3_766 . 110.0 ?
    C1 C5 H5B 3_766 . 110.0 ?
    N4 C8 H8A . . 109.9 ?
    N4 C8 H8B . . 109.9 ?
    N4 C8 C7 . . 108.9(2) ?
    H8A C8 H8B . . 108.3 ?
    C7 C8 H8A . . 109.9 ?
    C7 C8 H8B . . 109.9 ?
    N3 C6 H6A . . 109.3 ?
    N3 C6 H6B . . 109.3 ?
    N3 C6 C10 . 3_666 111.7(2) ?
    H6A C6 H6B . . 107.9 ?
    C10 C6 H6A 3_666 . 109.3 ?
    C10 C6 H6B 3_666 . 109.3 ?
    N3 C7 C8 . . 109.2(2) ?
    N3 C7 H7A . . 109.8 ?
    N3 C7 H7B . . 109.8 ?
    C8 C7 H7A . . 109.8 ?
    C8 C7 H7B . . 109.8 ?
    H7A C7 H7B . . 108.3 ?
    N1 C1 C5 . 3_766 108.9(2) ?
    N1 C1 H1A . . 109.9 ?
    N1 C1 H1B . . 109.9 ?
    C5 C1 H1A 3_766 . 109.9 ?
    C5 C1 H1B 3_766 . 109.9 ?
    H1A C1 H1B . . 108.3 ?
    C9 C10 C6 . 3_666 116.0(2) ?
    C9 C10 H10A . . 108.3 ?
    C9 C10 H10B . . 108.3 ?
    C6 C10 H10A 3_666 . 108.3 ?
    C6 C10 H10B 3_666 . 108.3 ?
    H10A C10 H10B . . 107.4 ?
    N1 C2 H2A . . 109.2 ?
    N1 C2 H2B . . 109.2 ?
    N1 C2 C3 . . 112.1(2) ?
    H2A C2 H2B . . 107.9 ?
    C3 C2 H2A . . 109.2 ?
    C3 C2 H2B . . 109.2 ?
    N2 C4 H4A . . 109.3 ?
    N2 C4 H4B . . 109.3 ?
    N2 C4 C3 . . 111.8(3) ?
    H4A C4 H4B . . 107.9 ?
    C3 C4 H4A . . 109.3 ?
    C3 C4 H4B . . 109.3 ?
    C2 C3 H3A . . 108.2 ?
    C2 C3 H3B . . 108.2 ?
    C4 C3 C2 . . 116.2(2) ?
    C4 C3 H3A . . 108.2 ?
    C4 C3 H3B . . 108.2 ?
    H3A C3 H3B . . 107.4 ?
    O7 C11 H11A . . 109.5 ?
    O7 C11 H11B . . 109.5 ?
    O7 C11 H11C . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    Zn1 O1 N5 O3 . . . . -149.2(2) ?
    Zn1 O1 N5 O2 . . . . 30.9(4) ?
    Zn1 N2 C5 C1 . . . 3_766 -42.5(2) ?
    Zn1 N2 C4 C3 . . . . 57.8(3) ?
    Zn1 N1 C1 C5 . . . 3_766 41.5(2) ?
    Zn1 N1 C2 C3 . . . . -53.7(3) ?
    Zn2 O4 N6 O6 . . . . 164.3(2) ?
    Zn2 O4 N6 O5 . . . . -16.1(4) ?
    Zn2 N4 C9 C10 . . . . 56.1(3) ?
    Zn2 N4 C8 C7 . . . . -42.1(2) ?
    Zn2 N3 C6 C10 . . . 3_666 56.1(3) ?
    Zn2 N3 C7 C8 . . . . -40.1(2) ?
    N4 C9 C10 C6 . . . 3_666 -71.3(3) ?
    N4 C8 C7 N3 . . . . 57.2(3) ?
    N2 C4 C3 C2 . . . . -73.0(3) ?
    N1 C2 C3 C4 . . . . 70.0(3) ?
    C9 N4 C8 C7 . . . . -169.3(2) ?
    C5 N2 C4 C3 . . . . 178.6(2) ?
    C8 N4 C9 C10 . . . . 177.6(2) ?
    C6 N3 C7 C8 . . . . -168.6(2) ?
    C7 N3 C6 C10 . . . 3_666 179.3(2) ?
    C1 N1 C2 C3 . . . . -177.7(2) ?
    C2 N1 C1 C5 . . . 3_766 171.1(2) ?
    C4 N2 C5 C1 . . . 3_766 -168.2(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O2 . 1.00 2.08 2.995(3) 151.0 yes
    N2 H2 O5 3_666 1.00 2.60 3.497(4) 149.0 yes
    N2 H2 O6 3_666 1.00 2.14 3.036(4) 148.0 yes
    N3 H3 O5 . 1.00 2.06 2.931(3) 145.0 yes
    N4 H4 O3 . 1.00 2.06 2.977(3) 151.5 yes
    O7 H7 O1 . 0.86 2.38 3.144(3) 148 yes
    O7 H7 O3 . 0.86 2.18 2.966(3) 151.2 yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.362
_shelx_estimated_absorpt_T_max     0.823
